# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

 
data_1
 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H17 Cu N O9' 
_chemical_formula_weight          370.79

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cu'  'Cu'   0.3201   1.2651
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.4875(3)
_cell_length_b                    9.4303(3)
_cell_length_c                    10.4406(4)
_cell_angle_alpha                 78.225(2)
_cell_angle_beta                  84.542(3)
_cell_angle_gamma                 83.261(2)
_cell_volume                      714.78(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     2492
_cell_measurement_theta_min       2.68
_cell_measurement_theta_max       25.33
 
_exptl_crystal_description        plate
_exptl_crystal_colour             Blue 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.723          
_exptl_crystal_F_000              382
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.350
_exptl_crystal_size_mid           0.280
_exptl_crystal_size_min           0.220
_exptl_absorpt_coefficient_mu     1.575
_shelx_estimated_absorpt_T_min    0.609
_shelx_estimated_absorpt_T_max    0.723
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5 
_exptl_absorpt_correction_T_max   0.7
_exptl_absorpt_process_details    SADABS
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             5462
_diffrn_reflns_av_unetI/netI      0.0588
_diffrn_reflns_av_R_equivalents   0.0390
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          1.998
_diffrn_reflns_theta_max          25.385
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.983
_diffrn_measured_fraction_theta_full  0.991
_diffrn_reflns_Laue_measured_fraction_max    0.983
_diffrn_reflns_Laue_measured_fraction_full   0.991
_diffrn_reflns_point_group_measured_fraction_max   0.983
_diffrn_reflns_point_group_measured_fraction_full  0.991
_reflns_number_total              2594
_reflns_number_gt                 2181
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   'WinGX publication routines (Farrugia, 1999)'
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0517P)²+0.7946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2594
_refine_ls_number_parameters      224
_refine_ls_number_restraints      8
_refine_ls_R_factor_all           0.0553
_refine_ls_R_factor_gt            0.0439
_refine_ls_wR_factor_ref          0.1114
_refine_ls_wR_factor_gt           0.1047
_refine_ls_goodness_of_fit_ref    1.059
_refine_ls_restrained_S_all       1.065
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.7863(5) 1.0033(4) 0.7689(4) 0.0154(8) Uani 1 1 d . . . . .
C2 C 0.8110(5) 1.0932(4) 0.6327(3) 0.0126(8) Uani 1 1 d . . . . .
C3 C 0.8626(5) 1.2326(4) 0.6211(4) 0.0145(8) Uani 1 1 d . . . . .
H3 H 0.8834 1.2644 0.6965 0.017 Uiso 1 1 calc R U . . .
C4 C 0.8838(5) 1.3250(4) 0.5011(4) 0.0141(8) Uani 1 1 d . . . . .
H4 H 0.9208 1.4168 0.4962 0.017 Uiso 1 1 calc R U . . .
C5 C 0.8497(5) 1.2803(4) 0.3875(3) 0.0116(8) Uani 1 1 d . . . . .
C6 C 0.8672(5) 1.3846(4) 0.2567(4) 0.0154(8) Uani 1 1 d . . . . .
C7 C 0.7983(5) 1.1421(4) 0.3959(4) 0.0137(8) Uani 1 1 d . . . . .
H7 H 0.7775 1.1119 0.3197 0.016 Uiso 1 1 calc R U . . .
C8 C 0.7773(5) 1.0475(4) 0.5164(4) 0.0119(8) Uani 1 1 d . . . . .
C9 C 0.6685(5) 0.8437(4) 0.4325(4) 0.0150(8) Uani 1 1 d . . . . .
C10 C 0.6243(5) 0.6901(4) 0.4756(4) 0.0169(8) Uani 1 1 d . . . . .
H10A H 0.7065 0.6302 0.4261 0.020 Uiso 1 1 calc R U . . .
H10B H 0.5038 0.6854 0.4510 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6316(6) 0.6208(4) 0.6208(4) 0.0208(9) Uani 1 1 d . . . . .
H11A H 0.7536 0.6118 0.6449 0.031 Uiso 1 1 calc R U . . .
H11B H 0.5893 0.5261 0.6364 0.031 Uiso 1 1 calc R U . . .
H11C H 0.5564 0.6810 0.6725 0.031 Uiso 1 1 calc R U . . .
Cu1 Cu 0.67523(6) 0.77921(5) 0.96227(4) 0.01321(17) Uani 1 1 d . . . . .
H12A H 0.424(6) 0.919(4) 0.829(3) 0.020 Uiso 1 1 d D U . . .
H13A H 0.823(4) 0.522(5) 0.870(3) 0.020 Uiso 1 1 d D U . . .
H14A H 1.007(4) 0.740(5) 0.962(3) 0.020 Uiso 1 1 d D U . . .
H15A H 0.468(4) 0.638(4) 1.129(4) 0.020 Uiso 1 1 d D U . . .
H12B H 0.353(5) 0.874(4) 0.977(3) 0.020 Uiso 1 1 d D U . . .
H13B H 0.769(5) 0.481(4) 0.993(3) 0.020 Uiso 1 1 d D U . . .
H14B H 0.941(5) 0.681(3) 1.100(3) 0.020 Uiso 1 1 d D U . . .
H15B H 0.661(4) 0.625(4) 1.179(4) 0.020 Uiso 1 1 d D U . . .
N1 N 0.7230(4) 0.9083(3) 0.5256(3) 0.0158(7) Uani 1 1 d . . . . .
H1 H 0.7243 0.8547 0.6028 0.019 Uiso 1 1 calc R U . . .
O1 O 0.7697(3) 0.8683(3) 0.7816(2) 0.0135(6) Uani 1 1 d . . . . .
O2 O 0.7815(4) 1.0652(3) 0.8638(3) 0.0252(7) Uani 1 1 d . . . . .
O3 O 0.9456(4) 1.4953(3) 0.2507(3) 0.0209(6) Uani 1 1 d . . . . .
O4 O 0.7988(4) 1.3534(3) 0.1606(2) 0.0212(6) Uani 1 1 d . . . . .
O5 O 0.6550(4) 0.9052(3) 0.3166(3) 0.0266(7) Uani 1 1 d . . . . .
O12 O 0.4276(4) 0.8481(4) 0.9053(3) 0.0339(8) Uani 1 1 d D . . . .
O13 O 0.7277(4) 0.5338(3) 0.9220(3) 0.0208(6) Uani 1 1 d D . . . .
O14 O 0.9200(5) 0.7601(4) 1.0311(3) 0.0363(8) Uani 1 1 d D . . . .
O15 O 0.5652(5) 0.6894(4) 1.1413(3) 0.0449(9) Uani 1 1 d D . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 O2 1.244(5) . ?
C1 O1 1.272(5) . ?
C1 C2 1.506(5) . ?
C2 C3 1.392(5) . ?
C2 C8 1.422(5) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C5 C7 1.385(5) . ?
C5 C6 1.515(5) . ?
C6 O3 1.244(5) . ?
C6 O4 1.270(5) . ?
C7 C8 1.393(5) . ?
C7 H7 0.9300 . ?
C8 N1 1.401(5) . ?
C9 O5 1.238(4) . ?
C9 N1 1.363(5) . ?
C9 C10 1.493(5) . ?
C10 C11 1.527(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
Cu1 O12 1.996(3) . ?
Cu1 O1 2.001(2) . ?
Cu1 O14 2.007(3) . ?
Cu1 O15 2.028(4) . ?
Cu1 O13 2.417(3) . ?
N1 H1 0.8600 . ?
O12 H12A 0.931(19) . ?
O12 H12B 0.945(19) . ?
O13 H13A 0.865(19) . ?
O13 H13B 0.867(19) . ?
O14 H14A 0.955(19) . ?
O14 H14B 0.936(19) . ?
O15 H15A 0.948(19) . ?
O15 H15B 0.947(19) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 C1 O1 123.0(3) . . ?
O2 C1 C2 118.3(3) . . ?
O1 C1 C2 118.7(3) . . ?
C3 C2 C8 118.1(3) . . ?
C3 C2 C1 117.5(3) . . ?
C8 C2 C1 124.3(3) . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C7 C5 C4 119.5(3) . . ?
C7 C5 C6 121.2(3) . . ?
C4 C5 C6 119.3(3) . . ?
O3 C6 O4 124.4(3) . . ?
O3 C6 C5 118.3(3) . . ?
O4 C6 C5 117.4(3) . . ?
C5 C7 C8 121.3(3) . . ?
C5 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 N1 121.5(3) . . ?
C7 C8 C2 119.3(3) . . ?
N1 C8 C2 119.2(3) . . ?
O5 C9 N1 123.6(4) . . ?
O5 C9 C10 119.6(3) . . ?
N1 C9 C10 116.8(3) . . ?
C9 C10 C11 118.1(3) . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10B 107.8 . . ?
C11 C10 H10B 107.8 . . ?
H10A C10 H10B 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 Cu1 O1 87.57(12) . . ?
O12 Cu1 O14 165.46(14) . . ?
O1 Cu1 O14 91.89(12) . . ?
O12 Cu1 O15 89.24(14) . . ?
O1 Cu1 O15 176.66(13) . . ?
O14 Cu1 O15 91.45(15) . . ?
O12 Cu1 O13 104.05(12) . . ?
O1 Cu1 O13 93.65(10) . . ?
O14 Cu1 O13 90.48(12) . . ?
O15 Cu1 O13 86.16(13) . . ?
C9 N1 C8 130.7(3) . . ?
C9 N1 H1 114.6 . . ?
C8 N1 H1 114.6 . . ?
C1 O1 Cu1 112.7(2) . . ?
Cu1 O12 H12A 114(3) . . ?
Cu1 O12 H12B 109(2) . . ?
H12A O12 H12B 114(4) . . ?
Cu1 O13 H13A 112(3) . . ?
Cu1 O13 H13B 106(3) . . ?
H13A O13 H13B 98(4) . . ?
Cu1 O14 H14A 107(2) . . ?
Cu1 O14 H14B 114(3) . . ?
H14A O14 H14B 104(4) . . ?
Cu1 O15 H15A 109(3) . . ?
Cu1 O15 H15B 103(3) . . ?
H15A O15 H15B 111(4) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O2 C1 C2 C3 12.5(5) . . . . ?
O1 C1 C2 C3 -168.2(3) . . . . ?
O2 C1 C2 C8 -164.5(4) . . . . ?
O1 C1 C2 C8 14.8(5) . . . . ?
C8 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C4 -178.1(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C4 C5 C7 -1.3(5) . . . . ?
C3 C4 C5 C6 177.9(3) . . . . ?
C7 C5 C6 O3 -166.6(3) . . . . ?
C4 C5 C6 O3 14.1(5) . . . . ?
C7 C5 C6 O4 14.1(5) . . . . ?
C4 C5 C6 O4 -165.2(3) . . . . ?
C4 C5 C7 C8 1.0(5) . . . . ?
C6 C5 C7 C8 -178.2(3) . . . . ?
C5 C7 C8 N1 179.1(3) . . . . ?
C5 C7 C8 C2 -0.7(5) . . . . ?
C3 C2 C8 C7 0.6(5) . . . . ?
C1 C2 C8 C7 177.6(3) . . . . ?
C3 C2 C8 N1 -179.2(3) . . . . ?
C1 C2 C8 N1 -2.2(5) . . . . ?
O5 C9 C10 C11 -176.4(3) . . . . ?
N1 C9 C10 C11 3.9(5) . . . . ?
O5 C9 N1 C8 -1.4(6) . . . . ?
C10 C9 N1 C8 178.3(3) . . . . ?
C7 C8 N1 C9 -6.0(6) . . . . ?
C2 C8 N1 C9 173.8(4) . . . . ?
O2 C1 O1 Cu1 14.3(4) . . . . ?
C2 C1 O1 Cu1 -165.0(2) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O15 H15A O13  0.948(19) 2.48(2) 3.406(5) 166(4) 2_667
C7 H7 O5  0.93 2.26 2.883(5) 124.2 .
N1 H1 O1  0.86 1.96 2.673(4) 139.4 .
O14 H14B O3  0.936(19) 2.10(2) 3.027(4) 171(4) 1_546
O14 H14A O4  0.955(19) 2.08(2) 3.021(5) 166(4) 2_776
O15 H15B O3  0.947(19) 2.43(2) 3.363(5) 169(4) 1_546
O12 H12A O5  0.931(19) 2.08(2) 2.982(4) 164(4) 2_676
O12 H12B O2  0.945(19) 2.01(2) 2.953(4) 174(4) 2_677
O13 H13B O4  0.867(19) 1.92(2) 2.773(4) 166(4) 1_546
O13 H13A O3  0.865(19) 2.05(2) 2.918(4) 177(4) 2_776
 
_refine_diff_density_max    0.638
_refine_diff_density_min   -0.566
_refine_diff_density_rms    0.109

_shelxl_version_number 2014-1



